EP0912533B1 - Alkylaminobenzothiazole und -benzoxazole derivate - Google Patents

Alkylaminobenzothiazole und -benzoxazole derivate Download PDF

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Publication number
EP0912533B1
EP0912533B1 EP97923913A EP97923913A EP0912533B1 EP 0912533 B1 EP0912533 B1 EP 0912533B1 EP 97923913 A EP97923913 A EP 97923913A EP 97923913 A EP97923913 A EP 97923913A EP 0912533 B1 EP0912533 B1 EP 0912533B1
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Prior art keywords
formula
compounds
alkyl
compound
hydrogen
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EP97923913A
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English (en)
French (fr)
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EP0912533A1 (de
Inventor
Ludo Edmond Josephine Kennis
Josephus Carolus Mertens
Serge Maria Aloysius Pieters
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Janssen Pharmaceutica NV
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Janssen Pharmaceutica NV
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Priority to EP97923913A priority Critical patent/EP0912533B1/de
Priority to EP03075959A priority patent/EP1325917B1/de
Publication of EP0912533A1 publication Critical patent/EP0912533A1/de
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42—Oxazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/002—Heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D277/82—Nitrogen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Psychiatry (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Claims (9)

  1. Verbindungen der Formel
    Figure 00350001
    deren N-Oxidformen, pharmazeutisch unbedenkliche Säureadditionssalze und stereochemisch isomere Formen, wobei
    X
    für O oder S steht;
    n
    für 2, 3, 4 oder 5 steht;
    R1
    für Wasserstoff, C1-6-Alkyl, C1-6-Alkyloxy oder Halogen steht;
    R2
    für Wasserstoff, C1-6-Alkyl, Phenyl, Phenyl-C1-6-alkyl oder Phenylcarbonyl steht;
    R3 und R4
    jeweils unabhängig voneinander aus Wasserstoff, Halogen, Nitro, C1-6-Alkyl, C1-6-Alkyloxy, Halogen-C1-6-alkyl, Aminosulfonyl, Mono- oder Di-(C1-4-alkyl)aminosulfonyl ausgewählt sind; oder
    R3 und R4
    auch zusammen einen zweiwertigen Rest der Formel -CH=CH-CH=CH- bilden können.
  2. Verbindungen nach Anspruch 1, wobei n für 2, 3 oder 4 steht.
  3. Verbindungen nach Anspruch 1 oder 2, wobei X für S steht und R2 für Wasserstoff, C1-6-Alkyl, Phenyl oder Phenyl-C1-6-alkyl steht.
  4. Verbindungen nach Anspruch 1 oder 2, wobei R2 und R3 für Wasserstoff stehen und R4 für Chlor steht.
  5. Verbindungen nach Anspruch 1, bei denen es sich um
    N-[2-[4-(3,4-Dichlorphenyl)-1-piperazinyl]ethyl]-2-benzothiazolamin;
    N-[2-(4-Phenyl-1-piperazinyl)ethyl]-2-benzothiazolamin;
    N-[2-[4-(4-Chlorphenyl)-1-piperazinyl]ethyl]-2-benzothiazolamin;
    N-[2-[4-(4-Bromphenyl)-1-piperazinyl]ethyl]-2-benzothiazolamin; und deren N-Oxide, deren stereoisomere Formen und deren pharmazeutisch unbedenkliche Säureadditionssalze handelt.
  6. Pharmazeutische Zusammensetzung, enthaltend einen pharmazeutisch unbedenklichen Träger und, als Wirkstoff, eine den Dopamin-D4-Rezeptor wirksam antagonisierende Menge einer Verbindung nach einem der Ansprüche 1 bis 5.
  7. Verfahren zur Herstellung einer pharmazeutischen Zusammensetzung nach Anspruch 6, dadurch gekennzeichnet, daß man einen pharmazeutisch unbedenklichen Träger innig mit einer den Dopamin-D4-Rezeptor wirksam antagonisierenden Menge einer Verbindung nach einem der Ansprüche 1 bis 5 mischt.
  8. Verbindung nach einem der Ansprüche 1 bis 5 zur Verwendung als Medizin.
  9. Verfahren zur Herstellung einer Verbindung nach Anspruch 1, dadurch gekennzeichnet, daß man
    a) ein Zwischenprodukt der Formel (III)
    Figure 00370001
    in welcher n und R2 bis R4 wie in Anspruch 1 definiert sind, mit einem Zwischenprodukt der Formel (II)
    Figure 00370002
    in welcher W für eine geeignete reaktive Abgangsgruppe steht und X und R1 wie in Anspruch 1 definiert sind, in einem reaktionsinerten Lösungsmittel, gegebenenfalls in Gegenwart einer geeigneten Base und gegebenenfalls in Gegenwart eines Katalysators, N-alkyliert;
    b) ein Zwischenprodukt der Formel (III)
    Figure 00370003
    in welchem n und R2 bis R4 wie in Anspruch 1 definiert sind, mit einem Zwischenprodukt der Formel (IV)
    Figure 00370004
    in welchem R1 wie in Anspruch 1 definiert ist, in einem reaktionsinerten Lösungsmittel und in Gegenwart von Thionylchlorid umsetzt und so eine Verbindung der Formel (I-a)
    Figure 00380001
    bildet;
    c) ein Zwischenprodukt der Formel (VI)
    Figure 00380002
    in welchem R3 und R4 wie in Anspruch 1 definiert sind, mit einem Zwischenprodukt der Formel (VII)
    Figure 00380003
    in welchem R1, R2, n und X wie in Anspruch 1 definiert sind und W2 für eine geeignete Abgangsgruppe steht, in einem reaktionsinerten Lösungsmittel N-alkyliert;
    d) ein Zwischenprodukt der Formel (XV)
    Figure 00380004
    in welchem X, R1 und R2 wie in Anspruch 1 definiert sind, mit einem Zwischenprodukt der Formel (XVI)
    Figure 00380005
    in welchem n, R3 und R4 wie in Anspruch 1 definiert sind und W2 für eine geeignete Abgangsgruppe steht, in einem reaktionsinerten Lösungsmittel in Gegenwart einer geeigneten Base N-alkyliert;
    e) Verbindungen der Formel (I) nach im Stand der Technik bekannten Transformationen ineinander umwandelt und weiterhin, falls gewünscht, die Verbindungen der Formel (I) durch Behandlung mit einer Säure in ein therapeutisch aktives, nichttoxisches Säureadditionssalz umwandelt oder umgekehrt die Säureadditionssalzform durch Behandlung mit Alkali in die freie Base umwandelt; und, falls gewünscht, stereochemisch isomere Formen oder N-Oxide davon herstellt.
EP97923913A 1996-05-10 1997-05-02 Alkylaminobenzothiazole und -benzoxazole derivate Expired - Lifetime EP0912533B1 (de)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP97923913A EP0912533B1 (de) 1996-05-10 1997-05-02 Alkylaminobenzothiazole und -benzoxazole derivate
EP03075959A EP1325917B1 (de) 1996-05-10 1997-05-02 Radiomarkierte Alkylamino-benzothiazole und -benzothiazole sowie ihre Verwendung als D4-Liganden

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP96201282 1996-05-10
EP96201282 1996-05-10
EP97923913A EP0912533B1 (de) 1996-05-10 1997-05-02 Alkylaminobenzothiazole und -benzoxazole derivate
PCT/EP1997/002505 WO1997043271A1 (en) 1996-05-10 1997-05-02 Alkylaminobenzothiazole and -benzoxazole derivatives

Related Child Applications (1)

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EP03075959A Division EP1325917B1 (de) 1996-05-10 1997-05-02 Radiomarkierte Alkylamino-benzothiazole und -benzothiazole sowie ihre Verwendung als D4-Liganden

Publications (2)

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EP0912533A1 EP0912533A1 (de) 1999-05-06
EP0912533B1 true EP0912533B1 (de) 2004-09-29

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EP97923913A Expired - Lifetime EP0912533B1 (de) 1996-05-10 1997-05-02 Alkylaminobenzothiazole und -benzoxazole derivate
EP03075959A Expired - Lifetime EP1325917B1 (de) 1996-05-10 1997-05-02 Radiomarkierte Alkylamino-benzothiazole und -benzothiazole sowie ihre Verwendung als D4-Liganden

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US (2) US6103725A (de)
EP (2) EP0912533B1 (de)
JP (1) JP3237759B2 (de)
KR (1) KR100330699B1 (de)
CN (1) CN1074766C (de)
AR (1) AR007079A1 (de)
AT (2) ATE277917T1 (de)
AU (1) AU710175B2 (de)
BG (1) BG64097B1 (de)
BR (1) BR9709065A (de)
CA (1) CA2253453C (de)
CZ (1) CZ295639B6 (de)
DE (2) DE69737217T2 (de)
EA (1) EA001360B1 (de)
EE (1) EE03563B1 (de)
ES (2) ES2230605T3 (de)
HK (2) HK1057044A1 (de)
HU (1) HUP9902993A3 (de)
ID (1) ID16889A (de)
IL (1) IL126968A0 (de)
MY (1) MY117852A (de)
NO (1) NO311027B1 (de)
NZ (1) NZ332309A (de)
PL (1) PL190721B1 (de)
SK (1) SK282919B6 (de)
TR (1) TR199802253T2 (de)
TW (1) TW593290B (de)
WO (1) WO1997043271A1 (de)
ZA (1) ZA974053B (de)

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IT1293804B1 (it) 1997-08-01 1999-03-10 Recordati Chem Pharm Diarilalchilpiperazine attive sulle basse vie urinarie
US6281216B1 (en) * 1998-02-09 2001-08-28 Duphar International Research B.V. 2-aminoquinoline derivatives having d4-agonistic activity
EP0982030A3 (de) 1998-08-17 2000-05-10 Pfizer Products Inc. 2,7-substituierte Octahydropyrrolo(1,2-a)pyrazinderivate als 5ht 1a Liganden
EP1117663A2 (de) * 1998-09-30 2001-07-25 Neurogen Corporation 2-piperazinoalkylaminobenzoazol derivate: dopamin rezeptor subtyp spezifische liganden
US6284759B1 (en) * 1998-09-30 2001-09-04 Neurogen Corporation 2-piperazinoalkylaminobenzo-azole derivatives: dopamine receptor subtype specific ligands
US6107313A (en) * 1998-10-02 2000-08-22 Combichem, Inc. Dopamine receptor antagonists
AU5569800A (en) * 1999-06-30 2001-01-31 Santen Pharmaceutical Co. Ltd. Brain sigma-1 receptor-binding ligand
AU2001249679A1 (en) 2000-03-31 2001-10-15 Ortho-Mcneil Pharmaceutical, Inc. Phenyl-substituted imidazopyridines
US6436939B2 (en) 2000-03-31 2002-08-20 Ortho-Mcneil Pharmaceutical, Inc. Method for using 2-aryloxyalkylaminobenzoxazoles and 2-aryloxyalkylaminobenzothiazoles as H3 antagonists
GB0203299D0 (en) * 2002-02-12 2002-03-27 Glaxo Group Ltd Novel compounds
CA2497827A1 (en) * 2002-09-06 2004-03-18 Janssen Pharmaceutica, N.V. (1h-benzoimidazol-2-yl)-(piperazinyl)-methanone derivatives and related compounds as histamine h4-receptor antagonists for the treatment of inflammatory and allergic disorders
EP2610234A1 (de) * 2004-02-24 2013-07-03 The General Hospital Corporation Katalytische Radiofluorierung
US8257680B1 (en) 2004-02-24 2012-09-04 The General Hospital Corporation Catalytic radiofluorination
US9017724B2 (en) 2004-02-24 2015-04-28 The General Hospital Corporation Catalytic radiofluorination
FR2877005A1 (fr) * 2004-10-22 2006-04-28 Bioprojet Soc Civ Ile Nouveaux derives d'arylpiperazine
US7731940B2 (en) 2006-01-25 2010-06-08 The Regents Of The University Of California Compositions and methods related to serotonin 5-HT1A receptors
EP2268647B1 (de) 2008-03-21 2017-01-25 The General Hospital Corporation Verbindungen und zusammensetzungen für den nachweis und die behandlung von morbus alzheimer und verwandten erkrankungen
CN109843293A (zh) * 2016-08-26 2019-06-04 百时美施贵宝公司 吲哚胺2,3-双加氧酶的抑制剂及其使用方法
PT109740B (pt) 2016-11-14 2020-07-30 Hovione Farmaciencia Sa Processo para a preparação de brometo de umeclidínio
KR20210091865A (ko) * 2020-01-14 2021-07-23 서울대학교산학협력단 혈관생성 저해 효과를 가지는 n-페닐벤조티아졸-2-아민 화합물 및 그를 포함하는 약제학적 조성물

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NZ332309A (en) 1999-08-30
KR20000005227A (ko) 2000-01-25
EE9800378A (et) 1999-04-15
EA199801000A1 (ru) 1999-04-29
HUP9902993A3 (en) 2002-01-28
ES2279923T3 (es) 2007-09-01
CN1218461A (zh) 1999-06-02
AU2956097A (en) 1997-12-05
EP1325917A1 (de) 2003-07-09
CA2253453A1 (en) 1997-11-20
ATE277917T1 (de) 2004-10-15
NO311027B1 (no) 2001-10-01
PL329849A1 (en) 1999-04-12
US6103725A (en) 2000-08-15
HK1018457A1 (en) 1999-12-24
NO985227D0 (no) 1998-11-09
NO985227L (no) 1999-01-11
DE69730962D1 (de) 2004-11-04
PL190721B1 (pl) 2005-12-30
BR9709065A (pt) 1999-08-03
MY117852A (en) 2004-08-30
DE69737217T2 (de) 2007-11-08
US6224849B1 (en) 2001-05-01
IL126968A0 (en) 1999-09-22
BG102819A (en) 1999-08-31
TW593290B (en) 2004-06-21
DE69737217D1 (de) 2007-02-15
ID16889A (id) 1997-11-20
SK153298A3 (en) 1999-03-12
HK1057044A1 (en) 2004-03-12
JP3237759B2 (ja) 2001-12-10
WO1997043271A1 (en) 1997-11-20
DE69730962T2 (de) 2006-03-30
EP1325917B1 (de) 2007-01-03
TR199802253T2 (xx) 1999-02-22
CZ355398A3 (cs) 1999-02-17
AR007079A1 (es) 1999-10-13
KR100330699B1 (ko) 2002-08-27
ES2230605T3 (es) 2005-05-01
CN1074766C (zh) 2001-11-14
EA001360B1 (ru) 2001-02-26
ZA974053B (en) 1998-11-09
ATE350373T1 (de) 2007-01-15
CZ295639B6 (cs) 2005-09-14
BG64097B1 (bg) 2003-12-31
AU710175B2 (en) 1999-09-16
CA2253453C (en) 2007-01-16
HUP9902993A2 (hu) 2000-05-28
EP0912533A1 (de) 1999-05-06
JP2000503667A (ja) 2000-03-28
SK282919B6 (sk) 2003-01-09
EE03563B1 (et) 2001-12-17

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